Akeem Jenkins

Hello, I'm Akeem Jenkins

Engineer, founder, lifter, father. Building optionality across software, business, and body.

I believe that technology is one of the greatest enablers of humanity. Whether it's something simple like the light bulb or as complex as a space shuttle, the constant pulse of advancing technology transforms the lives of every human on the planet.

AI

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Skills (and gaps)

I'd rather be explicit than over-claim. Here's what I'm strong at, what I'm growing, and what I'm not.

Strong

Areas where I'm confident delivering outcomes.

Information SecuritySecurity LeadershipOrg-wide ownership (IT + Cloud + Security + Product + Engineering)Budget ownership ($1M+/yr CAPEX/OPEX)Vendor management & contract negotiation (100+ vendors)Cloud SecurityAWS (EKS, EC2, S3, IAM, ALB/ELB, API Gateway, SSO, ECR, Security Hub)TerraformAWS Control TowerAWS Well-Architected FrameworkDevSecOpsCI/CD (GitHub Actions, Xcode Cloud, self-hosted runners)CI pipeline authoring & platform engineeringGitHub Advanced Security (GHAS)KubernetesArgoCD (GitOps)Container Security (ECR/images)DockerIdentity & Access Management (Okta, SSO, CASB)Identity migrations (Okta → Rippling)Encryption & Encryption SDK development (Go)GRC (ISO 27001, ISO 27701, SOC 2 Type 1 & 2, PCI/DSS)Compliance Automation (Drata)Compliance program ownership (Series A → Series B)SOC 2 engineering controls enforcementApplication SecuritySupply Chain SecurityIncident Response & InvestigationWAF / IDS / IPSSASE / ZTNACloudflare (security gateway, Workers, edge compute, WAF, API protection)Linux (RedHat, Ubuntu, Fedora, SUSE)Bug bounty program ownership (HackerOne)Penetration testingObservability strategy & rollout (Datadog)Cloud security posture management (Wiz - 0 Critical Club)Scaling infra from 0 → 250k+ paying usersGo (Golang)Swift / SwiftUI (macOS + iOS native app development)PythonKotlin (Android native development, Jetpack Compose)AI-native application architecture (agent loops, tool-use systems, streaming inference)LLM application development (Claude, GPT, multi-model routing via OpenRouter)Prompt engineering & system prompt architectureAgent loop design with tool orchestration (50+ tools across platforms)Knowledge graph memory systems (entity extraction, wiki-linking, FTS5, pgvector)Context window management & compaction strategiesAI safety & prompt injection defense (content sanitization, boundary tagging)Agent-first CLI design (schema manifests, NDJSON output, typed error envelopes, stable exit-code enums, stderr sanitization)Go CLI development (Cobra, single-binary stdlib-only distribution, Homebrew packaging)Android development (Kotlin, Jetpack Compose, Hilt DI, Room DB, Material 3)iOS development (Swift 6, SwiftUI, SwiftData, strict concurrency)Cross-platform feature parity management (Android + iOS)Full-stack mobile product architecture (dual-platform)Supabase (Auth, Edge Functions, Realtime, Row-Level Security)PostgreSQL (pgvector, scheduled agents, credit ledger, migration management)MCP (Model Context Protocol) server developmentIn-app purchase architecture (Google Play Billing, Adapty SDK, Stripe)Credit-based monetization systemsGo-to-market strategy for consumer AI productsUnit economics modeling for AI/LLM inference costsProduct management & backlog prioritizationIT Operations (ITIL, JIRA Service Management)Agentic & AI tooling (Claude, Cursor, Gemini - increased org output by 25%)Networking fundamentals (TCP/IP, DHCP, VPN, NSX)VMware vSphere / NSX / vCloud DirectorHybrid cloud architecture (VMware + AWS)Post-Quantum Cryptography (Kyber768, Dilithium 2)Cryptographic AgilitySelf-replicating systems (security research)Patent development (15+ patents, 13+ granted - cryptographic agility, PQC, distributed systems)C-level executive engagementPresenting to VCsPublic speaking / conference presentationsAgile / ScrumTeam leadership (up to 10 engineers/direct reports)Bilingual English/Japanese (business/professional level)HRIS / IT platform migrations (Okta → Rippling)Rippling (HRIS + IT platform)

Moderate

I've shipped here, but I'm not pretending it's my core identity.

TypeScript / Deno (edge functions)Python backend (asyncio, asyncpg, Starlette, APScheduler)Edge function development (Deno/TypeScript)Background processing (Android WorkManager, iOS BGProcessingTask/BGAppRefreshTask)Push notifications & proactive engagement systemsOAuth/authentication flows (Google Sign-In, Supabase Auth, ASWebAuthenticationSession)RAG patterns (memory search, FTS5 indexing, pgvector embeddings)Local / on-device LLM inference (Ollama, Gemma) for private classification workloadsIMAP integration & email automation (Proton Mail Bridge, local mail pipelines)Knowledge-graph tooling (Open Knowledge Format / okf, graph + backlink modeling)LLM-driven classification pipelines (taxonomy design, alias normalization, checkpointed state)Frustration detection & sentiment analysis in AI interactionsConversational UI design for AI assistantsOnboarding flow design (progressive disclosure, personality customization)Analytics pipeline architecture (event tracking, funnel state machines)Churn prediction via frustration signal correlationA/B testing paywalls and pricing strategiesWebhook-driven purchase verification pipelinesApp signing & store deployment automation (AAB → Play Console)Node.jsMicroservices architectureDistributed systems architectureOffensive security tooling (CVE exploitation, network scanning, brute-forcing)Big data correlation & API integrationSecurity tooling (Wiz, AWS Security Hub, Mayhem, GHS)GitLabGoogle CloudInternal IT program buildout (tickets, onboarding, asset lifecycle)People management (director + security engineer)SaltStack (configuration management)ELK stack (centralized log analysis)Blockchain / Cardano (stake pool operation, Terraform deployment, FIPS 140-2 cold storage)Data center design & operations (15 MW scale, custom shipping container infrastructure)Cryptocurrency mining (PoW hardware, AI trading bots)EDI integrationVMware View (Horizon)Healthcare IT solutions engineeringAI/ML model implementation (security AI for spam/phishing detection)

Familiar

Useful supporting skills I can lean on as needed.

JavaPerlC/C++ (embedded firmware, printer firmware debugging)Visual BasicPHPXMLSQL / MySQLOpen source toolingOpenStackBash / Shell scriptingHyper-VKVMXenHP BladeSystem / InfiniBand (QDR/DDR)SAN / iSCSI / NetApp storage / HP Storage (MSA, EVA)NetSuite ERPThreadX RTOS (embedded OS profiling)BitBucketHP-UX (UNIX)Windows Server / Active DirectoryMicrosoft AzureFastlane-adjacent automationDark mode / high contrast accessibilityMaterial 3 & iOS Human Interface Guidelines

Gaps

Areas where I have less depth today (and won't waste your time).

ML model training / research (beyond applied/security use-cases)Marketing (growth, demand gen, brand)Legal (contracts, corporate law)Finance (accounting, FP&A)

About Me

A passionate technologist with a diverse background from startups to the fortune 500

Professional Background

Currently, I work at Cloaked, a security and privacy company, where I serve as Senior Director of Information Security. My role encompasses a wide range of responsibilities including encryption, compliance, IT infrastructure, DevSecOps, and overall security.

Outside of work, I build mobile-first AI applications - dual-platform (Android + iOS) AI-native products with agent loops, tool-use systems, and streaming inference. It's where I push the boundaries of what LLMs can do on mobile devices.

I've had the privilege of being part of several startups throughout my career, each venturing into distinct domains - from privacy platforms to Bitcoin mining solutions, kitchen equipment sales, and blockchain infrastructure. These experiences have taught me that startups can serve as fertile grounds for learning and connecting seemingly unrelated topics, while building diverse skill sets and broadening understanding of various industries.

Personal Interests & Hobbies

Japan & Japanese language
Cardano (ADA 4 Life)
Gardening & sustainable living
Solar Power and Batteries
Camping
Grip Sport & Armlifting (GSI Super Series)

Philosophy

I believe that technology is one of the greatest enablers of humanity. Whether it's something simple like the light bulb or as complex as a space shuttle, the constant pulse of advancing technology transforms the lives of every human on the planet.

Projects

A mix of digital and physical projects that reflect my diverse interests

Digital Bits

AI Mobile Assistant

Active

A mobile-first AI assistant with dual-platform Android + iOS native apps. Features agent loops with 50+ tools, knowledge graph memory with entity extraction and wiki-linking, streaming inference, credit-based monetization, and proactive engagement systems.

KotlinJetpack ComposeSwift 6SwiftUISupabasePostgreSQLpgvectorClaude APIMCP

Higgs - Agent-First Proton Mail CLI

Open Source

An agent-first command-line interface for Proton Mail, written in Go. Every design decision targets language-model control over human convenience: a JSON schema manifest for tool discovery, NDJSON on stdout, typed error envelopes, and a stable exit-code enum agents can branch on. It connects to Proton Mail Bridge over IMAP and classifies mail through a local Ollama model into an 11-label taxonomy - your email never leaves your hardware.

GoCobraIMAPProton Mail BridgeOllamaLocal LLMSQLiteNDJSON
View on GitHub

okf - Open Knowledge Format CLI

Open Source

A vendor-neutral, agent-first Go CLI for the Open Knowledge Format - create, validate, lint, index, search, and graph knowledge bundles stored as plain markdown with YAML frontmatter. One static binary with zero runtime dependencies: where Google's reference OKF implementation is Python + Gemini + BigQuery, okf runs anywhere and is driven entirely by machine-readable `okf schema` output, JSON-by-default responses, and structured error envelopes - so any AI agent can operate the whole CLI without reading docs. Live at useokf.com.

GoKnowledge GraphsOKFAgentic CLIJSONstdlib-only
View on GitHub

ouracli - Agent-First Oura Ring CLI

Open Source

An agent-first CLI for the Oura Ring API v2, in Go. Built for language-model callers first: stdout always carries JSON - a single document, an NDJSON stream, or a typed error envelope, never prose - and every subcommand is self-describing via `oura schema`. One endpoint registry drives the CLI, the schema manifest, and a built-in MCP server (`oura mcp serve`), so the three can never drift apart. Tokens live in the OS keyring (or an AES-256-GCM encrypted file), so secrets never touch the agent's context. Unofficial, community-built.

GoOura API v2MCPNDJSONOS KeyringAgent-First
View on GitHub

JAMF FileVault Recovery Key Extractor

Open Source

A Go-based tool for extracting FileVault recovery keys from JAMF Pro. Features automatic computer discovery, dual API support, comprehensive audit logging, and CSV report generation for IT administrators.

GoJAMF Pro APIFileVaultmacOS SecurityIT Administration
View on GitHub

Security & Privacy Tools

Active

Developing encryption and compliance tools at Cloaked, focusing on protecting user data and ensuring regulatory compliance.

EncryptionComplianceDevSecOpsIT Security

Open Source Contributions

Ongoing

Contributing to various open source projects in the security and privacy space.

GitHubSecurityPrivacyOpen Source

Websites

ARX Locations
Live

A location-based service platform providing comprehensive location data and services.

Visit arxlocations.com
FastList
Live

An agentic, next-generation classified site built on the Model Context Protocol (MCP). Post, browse, and interact with listings using AI assistants or agents. Features instant photo posting, zip code-based listings, and seamless integration with LLMs.

MCPAI IntegrationClassifiedsAPI
Visit fastlist.org
okf - Open Knowledge Format
Live

A vendor-neutral, agent-first CLI for building and managing knowledge graphs in the Open Knowledge Format. A single Go binary that speaks JSON natively and is designed to be driven by any AI agent - schema discovery, typed error envelopes, and deterministic exit codes, with no Python runtime, cloud APIs, or vendor lock-in.

GoKnowledge GraphsAgentic CLIJSONOKF
Visit useokf.com
ouracli - Oura Ring CLI
Live

An agent-first CLI for the Oura Ring API v2, in Go. JSON always on stdout, a self-describing schema manifest, and a built-in MCP server driven from one endpoint registry. Tokens stay in the OS keyring, so secrets never touch the agent context.

GoOura API v2MCPAgent-FirstCLI
Visit ouracli.com

Physical Things

Sustainable Garden

Active

Maintaining a productive garden with various vegetables and herbs, practicing sustainable farming methods.

Organic FarmingSustainabilityFood Production

Chicken Farming

Active

Raising chickens for eggs and meat, learning about animal husbandry and sustainable food production.

Animal HusbandrySustainable FarmingFood Security

Grip Sport & Armlifting

Active

Training and competing in grip sport - raw finger, hand, wrist, and forearm strength. Following the Grip Sport International (GSI) framework and the Armlifting World Super Series: last-man-standing events like the Rolling Thunder and Saxon Bar deadlift, contested across weight classes with unlimited 60-second attempts and percentage-based scoring.

Grip StrengthArmliftingGSI Super SeriesARX / HIT

These projects represent my commitment to continuous learning and building things that matter.

Patents

14 patents in security, cryptography, and application protection technologies

Key Technology Areas

  • • Cryptographic agility & algorithm selection
  • • Post-quantum cryptography
  • • Dynamic security systems
  • • Application protection & self-replication
  • • Network security & vulnerability scanning
  • • Trusted execution environments
  • • Certificate management & auditing

Patent Portfolio

  • • 14 total patents (2021-2023)
  • • US and international (WO) filings
  • • Focus on real-world security challenges
  • • Innovation in legacy system integration

Content

Things I've published and written about

📝

Day One: Starting My Tirzepatide Journey

Health February 13, 2026 4 min read

Today is day one of tirzepatide. I took my first 2.5 mg shot this morning and wanted to write down what happened while it's fresh.

📝

The Operational Debt Crisis: Why AI-Generated Code Isn't Production-Ready

Technology October 24, 2025 8 min read

The explosion of AI-powered code generation has created a dangerous illusion: that building software has become trivially easy. But we've solved code generation while completely ignoring the operational burden that follows.

📝

Building an AI-Native API: A Three-Layer Architecture for the Agent Era

Technology October 18, 2025 8 min read

As AI agents become increasingly capable of discovering and consuming APIs autonomously, we need to rethink how we design our web services. Here's how I built an architecture specifically designed for AI discovery and consumption.

📝

Shifting Security Left: How LLMs and Agentic Coding Finally Make It Possible

Security September 17, 2025 12 min read

For years, "shifting security left" was more aspirational than practical. Now with LLMs and agentic coding, we can finally codify security best practices into every repository, catching vulnerabilities at the moment of code creation.

📝

Great Files for Programming: Inside Cursor's Development Workflow

Technology September 1, 2025 8 min read

Greg Isenberg interviews the VP of Cursor, who reveals the internal files and processes that make Cursor's development team so effective. From code review checklists to writing guidelines, here's what we can learn.

📝

Migrating from JAMF to Rippling: Why FileVault Key Escrow is Critical

Security January 16, 2025 5 min read

When transitioning from JAMF to Rippling MDM, escrowing FileVault recovery keys before shutting down JAMF is absolutely critical. Here's why I built a Go tool to automate this process and ensure no keys are lost during the migration.

📝

How LLMs Revolutionize Open Source Debugging: A pfSense Deep Dive Case Study

Technology September 19, 2024 8 min read

Before LLMs and Cursor, I wouldn't have dreamed of diving into a massive codebase like pfSense. But with AI assistance, I solved a complex Dynamic DNS issue in under 30 minutes by directly analyzing the source code.

📝

What Does it Mean to Startup?

Business November 1, 2023 4 min read

Throughout my career, I've had the privilege of being a part of several startups, each venturing into distinct domains, from kitchen equipment sales to Bitcoin mining solutions, cosmetics manufacturing, and software development in the security and privacy realm.

Get In Touch

Have a project in mind or want to collaborate? I'd love to hear from you.

Let's Connect

I'm always interested in discussing new opportunities, innovative projects, and ways to make technology work better for people.